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Summary

Entry #2 was posted on June 21, 2009.
It has the description "first encounter?"
It is tagged "marble" and "hornets".
In total, this clip is 1:36 long.

Footage from the Marble Hornets tapes. Alex is driving along a road at night, looking for a strange man he saw under a streetlamp. The footage cuts out as he is under the streetlamp, apparently unable to find the man. Jay suggests that the man he saw might be the same figure from Entry 1.

Entry #2
After a few more hours of tapes, I found this clip of Alex talking while driving.
For now, I will assume that this probably took place before the events of entry #1.

[00:13] Footage out the front window of a car driving at night. There is ambient noise, and Alex immediately begins to speak.
[00:13] Alex: "I got home late tonight and I was taking Rocky for his walk about, uh, twenty minutes ago, so around midnight. This was near the set of Marble Hornets. A little bit farther down the road we saw this really tall guy standing in the middle of the street, just completely still. For whatever reason, this really set off Rocky, and, um… he g— he got really scared. He… wouldn't move and he kept on pulling on his leash to go back home."
[00:38] A dot of light appears along the curve of the road, to the left of the screen. It gets larger as the car approaches. It is a tall streetlamp.
[00:38] Alex continues: "There was something about this guy that was just… it was strange. So, uh, we headed back home. I have a little bit of time left on this tape, and, um, I'm going to go see if he's still hanging around. In fact, I think this is the light he was standing under, so I'm going to go have a look here…"
[00:58] The top of the streetlight moves out of the top of the frame as the car comes in close.
[00:59] The car pulls off the side of the road into what appears to be a very small rest stop.
[01:02] The car comes to a halt. There are noises of a car door opening.
[01:03] The camera moves, as if it is being picked up.
[01:08] The visual pans to the road to the left of the car, and the ambient noise changes to nighttime outdoor noises. The camera is panning left and right.
[01:08] Alex says: "Okay, you can't really see it well on the camera, but… I don't see… anyone around here, so I guess he's… moved on. Uh… But, yeah, there's just something about that that—"
[01:23] The clip ends abruptly. Cut to black.
[01:25] White text on a black screen

The tape ends there.
From what he describes, I think he has seen something similar to the figure that appears in entry #1.

[01:33] Cut to black.
[01:35] Video ends.

Main Theories and Observations

This is possibly not the first time that Alex saw the Operator. It is possible that Entry 12 was the first encounter, and that Alex simply did not remember (or did not want to mention remembering) the events of 12 in this video.

The fact that he goes back with a camera to investigate a man standing on the side of the road would tend to support the idea that Alex already has an inkling that the Operator is something strange.

There is a possible Operator sighting in this video at 00:52, though this sighting is not widely agreed upon.

The cutting-out of the tape could be either:

The time on the tape running out (Alex mentions in the entry that he has a "little bit of time left on this tape").

Evidence of an Operator encounter interfering with the camera.

Further Speculation

This is probably the first time that the Slender Man is seen by Alex1. ~Dav Flamerock

This is a very early entry, chronologically, likely predating Entry #12, yet coming after entries #5 & #13; this cannot be determined conclusively, however. The fact that the recording ends abruptly is curious, & it perhaps implies that an encounter with the The Operator occured at that point. But it is also possible that Alex was simply using the end of some leftover footage from a Marble Hornets shoot to record his thoughts, as film students often do. This incident is likely when Alex began to take an (unhealthy) interest in the Slender Man.

~ Zeta Kai

*[According to the Wiki page for The Slender Man, it states that The Operator is not in Entry #2. He is, however, possibly there.

In case you have not seen him: turn the video to 420p(it helps a little)and set the screen to full size. At around the 40 second mark, you'll see the streetlight that Alex stops his car under. As Alex says, "I think this is the light he was standing under", focus your eyes to the left of the light. You will see a white blur appear moving upwards, and then snap to the right.

It distinctly looks like someone jerking their head up to look at Alex, or Alex's car, and then dart back out of sight.

Alex, obviously, does not notice it - it took me SEVERAL tries to see it, myself - but he is there.

~Lauren Hasty

Does this disprove the theory that TO is a forest deity? Why would the dog, a part of nature, be repelled from such a deity? I may be clutching at straws, but surely, its a possibility. ~ og1764